Why Your First Bet Is Always Wrong

Why Your First Bet Is Always Wrong

Far too often we fixate on optimizing the first idea we come across. We become emotionally attached to a single design, storyline, or hypothesis. The end result is a slow crawl towards incremental improvement. Our work becomes a shell of how good it could be if it were allowed to evolve.

The 5 Best Books to Help You Create More

Perennial Seller – Ryan Holiday

A useful starting place to understand the entire creative journey–from sitting down to create, through positioning, marketing, and building a platform. Holiday pulls dozens of examples from creative minds throughout history to uncover tactics and best practices. But the underlying strategy consistent throughout the book can be summed up as playing the long game. If you want to create something of lasting value, there are no shortcuts or paths to immediate gratification. Dedicate yourself to your creative process and put in the work.

To create something is a daring, beautiful act. The architect, the author, the artist–are all building something where nothing was before.
— Ryan Holiday

Grit – Angela Duckworth

In any creative endeavor, you’ll need both direction and determination–what Duckworth defines as “grit”– if you want to make meaningful progress. The book emphasizes the importance of deliberate practice, purpose, and stamina over intensity. The best thing about Duckworth’s writing is that she makes it real. It’s not about a magical experience that leads you to your passion, purpose, or life’s work. Instead, this comes through a discovery period–often messy, serendipitous, and inefficient–followed by years of refinement, and a lifetime of deepening.

Passion for your work is a little bit discovery, followed by a lot of development, and then a lifetime of deepening.
— Angela Duckworth

Atomic Habits – James Clear

Once you have a sense of direction, you need to build the creative habits to put things into action. The concept behind Atomic Habits is that by stacking tiny habits over time you can achieve compounding, remarkable results. Your creative results, as Clear suggests, are the lagging measure of your habits. He offers great insight into nonlinear growth (breakthrough moments), identity, discipline, and environmental design. The importance of building better systems is hard to overvalue. There’s room for everyone to improve in this capacity, and if nothing else it’s a refreshing reminder: “Does this behavior help me become the type of person I wish to be? Does this habit cast a vote for or against my desired identity?"

It is only by making the fundamentals in life easier that you can create the mental space needed for free thinking and creativity.
— James Clear

Creativity, Inc. – Ed Catmull

One of the best modern examples of the impact that comes from harnessing creativity and building a culture where the creative process can thrive. Catmull discusses the evolution of Pixar Animation, including the philosophies and strategies that have established them as creative force. Most notably, the team at Pixar embraces the years of ambiguity inherent to the creative process as a story evolves into its own. Instead of becoming attached to a single storyline or character, they seek out a deep truth at the core of the film–the guiding principle–and craft the story around that. Catmull also emphasizes the role of leadership in cultivating creativity. It starts with loosening your grip, accepting risk, trusting your people, and giving them space to do what they do best.

There is a sweet spot between the known and the unknown where originality happens; the key is to be able to linger there without panicking.”
— Ed Catmull

Leonardo da Vinci – Walter Isaacson

Throughout history there have been more profound, practical thinkers than Leonardo. But there’s never been anyone as creative as he was across so many different fields–art, science, engineering, technology, the humanities. If you’re hoping to improve your own creativity, you can do worse than studying the life and work of the person who became history’s archetype of the Renaissance Man. The depth of his curiosity and imagination are something to behold. What makes Leonardo such a powerful influence is that he was relatable and not some distant, untouchable figure. His creative genius was self-made, built from personal experience, experiments, and dedication to his craft.

Be open to mystery. Not everything needs sharp lines.
— Walter Isaacson

And One More…

If five books isn’t enough, check out Mastery by Robert Greene. It’s a comprehensive guide to living a creative life, and one of my favorites. Greene starts with the essentials–discovering your art and immersing yourself in the mindset of an apprentice–and tracks the journey through building creative strategies and, ultimately, mastery.

How the Stoics Mastered the Art of Influence

Desire for influence is human nature. Many people allow this to dictate the course of their lives, often unaware. But the Stoic philosophers developed a deeper sense of awareness and took the opposite approach.

Influence wasn’t their end goal. They approached it with indifference and chalked it up to fortune–nice to have but nonessential. Instead, they offered a more effective strategy–seek meaning over influence.

If you focus on work that matters to you and discover significance in yourself, you put yourself in a position to build something that strikes a deeper chord with others.

Find significance within yourself. Within your own sphere of power–that is where you have the greatest consequence.
— Epictetus

But if influence acts as your guiding principle, you dull your sense of authenticity and depth. You might get lucky and hit the target a few times. But you’ll always be guessing. And it’s difficult to sustain when you’re creating from outside of yourself and dependent on things beyond your control.

It’s a dangerous game to tie your sense of meaning and self-worth to external conditions. You introduce dependencies that can drop you into a state of anxiety, envy or despair, without warning.

Sooner or later your voice begins to waiver. By allowing influence to dictate your decisions, you compromise the quality of your work and your character. And how much good can you do if you sacrifice your integrity and a sense of meaning in your work along the way?

What you’re building must first resonate with you before you can expect it to resonate with anyone else.

But if you lose your honor in striving for greater (perceived) significance, you become useless.
— Epictetus

People gravitate towards those who have discovered a deeper sense of meaning in their work. That’s why the Stoics remain relevant to this day. They created from a place of meaning and valued their internal compass over recognition.

When you seek meaning over influence, you add an unusual depth to your voice that draws people in.

Epictetus, Marcus, and Seneca knew this well. They channeled their own sense of authenticity into their work and they way they lived their lives.

As their influence grew, they leveraged it to contribute something worthwhile. But they weren’t dependent on it. Despite the obstacles faced and privileges afforded, they remained focused on what was within their realm of control–living a meaningful life to the best of their ability.

Meaning starts with something that’s all your own. By prioritizing meaning over influence, you build the courage to speak from a place that resonates with you.

You would be foolish to ignore your audience entirely. But that’s a secondary consideration because there’s no guarantee. You’re the one who has to live with the work you put out into the world and the way you live your life.

Influence is far more likely to follow if you build something you believe in.

Keep your principles in order. When influence tilts your way, you’ll be prepared to lead with a steady hand like a Stoic. You’ll position yourself as the antithesis of the paranoid, corrupt leaders scattered throughout history.

But if you fail to assign things their proper value, you’ll risk losing yourself to an obsession with influence and power.

Focus instead on the things that are your own and create from there. There’s more fulfillment in this work and it often leads to better outcomes.

When you focus on your own authenticity, there’s a far greater chance it will resonate and make a measurable difference in someone else’s life. And even if it doesn’t, it remains valuable because it meant something to you. There’s a fundamental beauty in that.

Beautiful things of any kind are beautiful in themselves and sufficient to themselves. Praise is extraneous...Are any of those improved by being praised? Or damaged by contempt?
— Marcus Aurelius

It’s a rare thing in this world to first seek significance in yourself and build the courage to create something that resonates with you. Trust yourself. The world is drawn to authenticity.

When you value meaning over influence you’ll achieve a state of relaxed concentration to do the work that matters. The work you find meaning in. And it’s through this work that you build character and a sense of authenticity.

Seek meaning first, authenticity and influence will follow.
Seek influence first and you’ll risk losing yourself along the way.

*My original post appeared on Daily Stoic – a great resource for all things Stoicism. Check out their daily email for thought-provoking morning meditations.

9 Tactics to Help You Create More, Consume Less

When it comes to remarkable leaders, artists, scientists, and entrepreneurs, each individual has their own set of principles. But there is one underlying strategy that remains constant, revealing itself in different shades across each person–creating more and consuming less.

It’s through the work you put out into the world and the way you live your life that you build a sense of meaning. Smart creatives understand this in a deep way. By creating more, you claim a larger part of yourself.

Strategies like this help build energy, establish your identity, and inform the tactics you put in place. While it takes shape in different mediums, the overall strategy is to create more and consume less. It’s the mental framework which informs smaller decisions throughout the day.

Tactics are the individual pieces that comprise the larger whole. They differ in that they require an initial investment up front. It’s what you dedicate time and energy to on a daily basis to reinforce your strategy.

Author and habit expert, James Clear, explains habits as the individual votes you cast each day for a certain identity. The same concept applies here. Tactics are the individual votes you cast each day for a certain strategy. If your strategy is to create more and consume less, you need tactics to help encourage both.

1) Make it difficult to do the easy thing (consuming)

Adding resistance can be a powerful tactic. You want to make it harder to mindlessly consume. If you struggle with Netflix, unplug the television or sign out of your account after each use. If you struggle with social media, change your passwords at the start of each week and sign out of your accounts so you can’t easily access them.

It’s amazing how impactful it can be to move things out of plain sight. Whatever’s undermining your creative energy, add more resistance so you can redirect that towards something you find greater meaning in.

2) Make it easier to do the difficult thing (creating)

This is about environment design. Building something from nothing is difficult enough as is, don’t make it any harder on yourself. Prioritize time and space for your craft to reach a deeper level of focus and creativity.

For years, my place for creativity at home–where I would sit down to write–was a couch that faced the television in my living room. And to further compound the problem, I wasn’t attempting this during quieter hours of the day. It was while people were coming and going, stopping to watch Netflix, sitting down for a meal. There were incessant distractions.

But this past year, I carved out physical space dedicated to writing. I converted one of our bedrooms to a writing studio/library and it’s made a significant difference. I also started writing first thing in the morning while my mind is fresh and I have two quiet hours before work.

Dedicating time and space where you can focus without interruption on your craft will allow you to grow exponentially faster. It’s the first step towards taking yourself and your art seriously.

Make it easier to do the right thing. This doesn’t mean sitting around waiting for ideal conditions or until you’re completely prepared, otherwise you’ll be waiting forever. It means setting yourself up for success through the things you can control in your immediate environment.

3) Pair positive reinforcements

Four years ago, when I first started taking writing seriously, I paired my writing sessions with my favorite coffee shop in Nashville. I walked over in the evenings after work to sit down and write. It’s something I looked forward to every day because of the atmosphere, the music I would listen to and, of course, the caffeine. This reinforcement helped me rediscover writing as a creative outlet.

Now I automatically associate these cues with my creative process. Coffee, coffee shops, and ambient music are shortcuts that jump me into a state of relaxed concentration that I need to do my best writing.

4) Allow yourself to get stuck

At the first sign of boredom or discomfort, most of us instinctively search for distractions and outlets for immediate gratification. And we do so without even recognizing it.

Until recently, the moment I slowed down or felt stuck in my own writing, I coped by jumping between tabs in Chrome–checking email, looking up restaurants for dinner, scrolling through Twitter.

The secret is to allow yourself to get stuck and sit with something. Once I gave myself permission to sit there without looking away, my resilience and creativity improved immediately.

Momentum is easier to come by when you don’t look away at the first challenging moment. Bouncing between distractions won’t result in some magical insight. Give yourself permission to get stuck.

Too many people believe that everything must be pleasurable in life, which makes them constantly search for distractions and short-circuits the learning process. The pain is a kind of challenge your mind presents–will you learn how to focus and move past the boredom, or like a child will you succumb to the need for immediate pleasure and distraction.
— Robert Greene

For writers: Tools aren’t everything but they can be helpful. I’ve found Ulysses to be one of the best investments I’ve made ($5/month). It helps facilitate each of these first four tactics. Its typewriter mode is fullscreen which makes it easier to focus, harder to jump between distractions (web, email, text messages), and the daily goals feature helps create a strong positive reinforcement.

5) Create a distraction-free phone

For most of us, myself included, our phones are our number one source of distraction. Jake Knapp and John Zeratsky outline the tactic that is a distraction-free phone in their book Focus. It’s one of the most influential tactics I’ve found in the past year. There are three main components:

  1. Delete infinity-pools apps (social media) from your phone

  2. Delete email accounts from your phone

  3. Delete/disable the web browser on your phone

These might sound extreme, but let me explain. Last year I took step one, deleting infinity-pools apps (sources of never-ending streams of content). But the energy I wasted on social media was replaced by checking email, random websites, and Googling everything that crossed my mind.

It was only after I took steps two and three, despite my initial reservations, that I saw a measurable difference in my focus and creativity. There’s now far less clutter and distraction in my day-to-day. As a result, the clarity of my thoughts has improved and I have more opportunities to create.

I recognize this might strike terror in you. But test it out for a week and see how it goes. I no longer reach for my phone as a crutch in moments of boredom. And it taught me how many meaningless things cross my mind and how few emails (zero) require an immediate response.

6) Keep a journal instead

If you cut the time spent on your phone in half and replaced that with journaling, you’d improve your balance between creating and consuming within a matter of days. I leave a journal sitting on the table of whichever room I’m in at home. I jot down ideas as they come to me, intentions in the morning, reflections in the evening, beginnings of articles, and whatever else captures my curiosity.

The act of writing on paper allows you to explore concepts and draw connections in ways that you can’t on a screen. Your ideas take on a different dimension. Not to mention the fact that it eliminates the threat of distractions you face on a phone, tablet, or computer.

But the biggest advantage of journaling is that it helps build awareness. By reflecting, you gain insight into your own behaviors and tendencies, rather than wandering through life on autopilot. If you want to create more and consume less, you have to start by recognizing what you’re doing well and where there’s room to improve.

7) Use art as inspiration

This is not to say that you shouldn’t appreciate other people’s work. But you should use it as inspiration to create something of your own. Actively engage in the things you’re watching, reading, listening to, and consuming. Try to engage, form connections, and draw insights of your own. (Check out my book notes on 70+ titles for an example of how I approach this while reading.)

Use books, films, documentaries, paintings, research, and keynotes as inspiration to create more. If you’re a writer, weave one of the connections you made into your next article. If you’re an entrepreneur, adapt one of the stories to your current project and share it with your team to build stronger engagement.

The goal is to create an active mental landscape that’s alive with hundreds of connections. It directly benefits your creativity and craft when you’re able to combine ideas across disciplines in new and interesting ways.

8) Start small

Don’t go off the deep end and commit to twelve hours of creating each day. You’ll burn yourself out before you ever get started and make it difficult to recover. Instead, begin from a more sustainable place.

If you want to write more music, start with fifteen minutes each day then build from there. That’s how you create momentum. Develop habits that are sustainable and allow them to grow steadily over time.

Remind yourself that growth is nonlinear. Don’t expect immediate results. People tend to overestimate what they can accomplish in the short-term and underestimate what they can accomplish over the course of years. The power of small, calculated decisions and tactics grows exponentially over time. Start small and let compound interest run its course.

9) Find a medium that resonates with you

While every remarkable mind shares some sense of this strategy to create more and consume less, the medium varies. For J.K. Rowling it’s writing, Jay-Z it’s music, Scott Belsky it’s design and technology, Alexander von Humboldt it was exploration and science, Leonardo da Vinci it was art and engineering.

If you need a better starting place, consider the medium that resonates with you. Robert Greene, author of The Laws of Human Nature, suggests reflecting on three areas to help with this:

  1. Inclinations in your earliest years–moments of fascination with certain subject, objects, or activities.

  2. Moments when certain tasks or activities felt natural to you.

  3. Particular forms of intelligence your brain is wired for.

The key is determining what’s meaningful to you and not absorbing what’s important to someone else as your own. Otherwise, you’ll miss the mark.

This is perhaps the most difficult skill of all–sorting through the noise and determining your own sense of authenticity. This requires years of exploration and reflection to determine for yourself. But it’s the only way to sustain a creative mindset and find meaning in your work.


As a rule of thumb, it’s better to lean towards the mentality of a strategist than a tactician. Those who have the patience to expand their perspective of time and the endurance to play the long game put themselves at a significant advantage. There are multiple paths and hundreds of tactics you can use you reach the end goal.

These tactics are meant to help you find your own starting place. Use them to create momentum and discover what works best for you. Experiment and remain flexible. There’s no correct path or proper sequence of decisions. What matters is that the overall strategy to create more and consume less is held in constant focus.

The Philosophy of Remarkable Minds

Each of us has the capacity to face difficult work. In many ways, this defines life. The struggle to create something of our own is where we find meaning.

Our modern era of comfort and convenience can be a double-edged sword. It’s allowed us to eliminate the daily struggle for survival and afforded us the privilege of having this discussion. But when taken to an extreme, it leads to a deep anxiety and restlessness. Emptiness can be a fiercer foe than hardship.

Humans don’t mind hardship, in fact they thrive on it; what they mind is not feeling necessary.
— Sebastian Junger

It’s easy to sit by as a passive consumer and allow someone else to assume the risk. On a surface level, it might even appear that you’re reaping all the benefits. But if you fail to establish a creative outlet where you can build something of your own, you sacrifice your primary source of meaning along with it.

It’s through the work you put out into the world and the way you live that you instill your life with a sense of meaning. By creating more and consuming less you claim a larger part of yourself.

Those who have lived remarkable lives hold this philosophy in constant focus.

Into the Venezuelan Jungle

When Alexander von Humboldt was born in 1769 to a family of wealthy Prussian aristocrats, by all standards of the day, he had it made. His father was an army officer and advisor to King Friedrich Wilhelm II, and his mother was the daughter of a rich manufacturer. If he wanted a comfortable existence, all he had to do was sit back and stay the course.

But despite these advantages, he was anxious and unhappy for most of his early years. His adventurous spirit was never satisfied by the confines of a classroom or the promise of a lucrative career as a civil servant. His dream was to explore the natural world.

As a child, Humboldt was fascinated with the journals of Captain James Cook and his accounts of distant countries and cultures. Humboldt wandered the Berlin countryside to recreate adventures of his own, stuffing his pockets full of plants, rocks, and insects, earning the nickname ‘the little apothecary.’

But after his father died at the age of nine, his financial dependence on his emotionally distant mother allowed her to dictate much of the early, unfulfilling course of his life. Despite his objections, she demanded that he work his way up the ranks of the Prussian administration.

Humboldt found creative ways to channel his deep interest in science, geology, and languages at different universities and academies along the way. He poured over the work of various artists, botanists, explorers, and thinkers. And while each provided inspiration, it was not enough to fill the void he faced for the first twenty-seven years of his life.

Humboldt was torn between the expectations of his family and his insatiable desire to set sail, experience the world firsthand, and contribute something of his own to the scientific community. He lacked an outlet to discover and create in a way that resonated with him. Without this, an emptiness continued to build.

It was only after his mother’s death in 1796 that he felt in control of his own destiny. Longing to escape his tiny corner of the world, he began planning a voyage to South America.

At age thirty, Humboldt set off on the expedition which altered the course of his life. He would explore treacherous landscapes that no scientist had set foot in before. The driving force was his desire to piecing together a more cohesive understanding of the natural world. Most scientists of his day were focused on isolated disciplines. Humboldt was interested in bridging the divide and the interconnected whole.

After arriving in Venezuela, Humboldt trekked for two months across the tropical grasslands of Los Llanos, facing temperatures near 120 degrees Fahrenheit. He followed this with seventy-five days of grueling river travel down the Orinoco, covering 1400 miles to reach the Casiquiare canal–a natural tributary between the Orinoco and Amazon rivers. Along the way, he faced torrential rains, incessant mosquitos, the occasional jaguar, and bouts with fevers and dysentery.

This would seem disheartening to most, but Humboldt came alive with boundless energy and enthusiasm during these explorations. No matter the conditions, he insisted on measuring the height of mountains, determining longitude and latitude, taking temperatures of the air and water, making astronomical observations, collecting new species of plants, and documenting it all with detailed notes. Each new environment brought him closer to understanding how the natural world fit together.

The pinnacle of his experience in South America came during a 2,500-mile journey from Cartagena to Lima to explore the Andean Mountains. During this trip, he attempted to summit Chimborazo, an inactive volcano standing at 21,000 feet.

At 15,600 feet, the porters refused to go on. But Humboldt continued his ascent, fighting through freezing conditions, deep fields of snow, and altitude sickness. Without fail, every few hundred feet he stopped and fumbled with freezing hands to set up his instruments to measure temperature, humidity, altitude, and boiling points. He reached 19,286 feet–a world record at the time–before he was forced to turn around due to impassable conditions.

This experience inspired Humboldt to sketch ‘Naturgemälde,’ a depiction of Chimborazo’s cross sections with the distribution of vegetation, temperature, humidity, and atmospheric pressure according to altitude. Humboldt showed for the first time that nature was a global force with corresponding climate zones across continents. And he presented it in an unprecedented infographic style, allowing those without a scientific background to understand the concept.

Naturgemälde – Alexander von Humboldt’s first depiction of nature as an interconnected whole

Naturgemälde – Alexander von Humboldt’s first depiction of nature as an interconnected whole

Upon his return to Europe, Humboldt’s exploration of South America inspired him to write thousands of letters, essays, publications, and lectures. By making connections and framing nature as a unified whole, his work revolutionized the way we view the natural world. As an interesting aside, he was also the first to observe and describe human-induced climate change.

Humboldt inspired generations of scientists and writers including Charles Darwin, Henry David Thoreau, and John Muir. But his greatest contribution was making science more accessible and exciting to a broader audience.

In Berlin, his series of free lectures packed music and university halls with royal family, students, servants, women, and children. He took his audience on a journey that ignited their imagination–combining exact observation with painterly descriptions. He brought distant landscapes to life through poetry, geology, and astronomy, bridging the divide between art and science.

Humboldt continued exploration into his sixties with a 10,000 mile, six-month journey through Russia. He was invigorated by each expedition, showing the same youthful energy and endurance that he had thirty years earlier. He shared his learnings in publications and letters up until his final moments when he died in 1859 at the age of eighty-nine.

The Struggle to Create

Humboldt could have settled into his early existence, lived a comfortable life, and allowed others to assume the risk in their own research and exploration. But this shallow life wasn’t enough for him. Instead, he set out with an insatiable curiosity to better understand the natural world and contribute what he learned along the way.

His adventures were his outlet for creativity, discovery, and meaning. There’s nothing easy about a 2,500-mile trek through the Andes. But the struggle to study and create something that resonated with him at a deeper level brought him to life. Without this, he would have never found his own sense of authenticity and fulfillment.

Creativity is about finding something worth struggling for.

We live in a unique time. Most of us, like Humboldt, could coast through life without facing any significant hardship if we so chose. That’s a wonderful thing. But it collapses into its opposite when we allow our entire lives to be dictated by comfort and immediate gratification. We must not forget the importance of meaning, which is found through the struggle to create something of our own.

Spending the evening watching four episodes of your favorite show on Netflix or scrolling through Instagram might be the path of least resistance, but it’s mostly empty. There’s little opportunity to create meaning of your own. More often than not it’s a distraction that pulls you away from the things that actually matter.

Your unique identifiers are the work you put out into the world and the way you live your life. These are what add depth to your voice. Not the things you consume–fashion, film, food, music, research, sports, technology.

This is not to say that you shouldn’t appreciate other people’s original work. But you should use it as inspiration. It should serve as a catalyst for you to create more and find alignment in your own sense of authenticity. It’s the height of selfishness to expect other people to create meaningful work for your personal benefit without contributing anything of your own.

Creating begins with making yourself an essential part of the process. Not standing by as a passive consumer and allowing someone else to take the risk.

But don’t let anyone fool you, creating is challenging, uncomfortable, and a slow grind. There’s no way around it. That’s why most people fail to sustain the habit. You have to trust your capacity to suffer. But it’s where all the upside is found.

Endurance, Imagination, and Depth

When you prioritize creating something of your own, you give yourself more opportunities for peak experiences and claim a larger part of yourself–just as Humboldt did at the age of twenty-seven when he shifted the course of his life. This is infinitely more satisfying than the temporary highs of a consumer.

By creating more and consuming less, you add an unusual depth to your voice that draws people in. Your creative outlet is where you are able to channel the questions and struggles you’ve faced into something that offers profound insight. And that’s what life is all about.

Whether you forgo a life of privilege to trek through the Venezuelan jungle or you set aside Instagram so you can focus on your art, science, startup, or relationship with the person right in front of you, what matters is that you provide yourself an opportunity to create.

Those who make a measurable difference in the world are inspired to contribute something of their own. Instead of taking the easy route–opting for comfort and immediate gratification–they push themselves further into the unknown.

Human nature has given us remarkable endurance to face difficult work and the imagination to build something from nothing. It’s through this struggle to create that we instill our lives with a sense of meaning.

To find your sense of authenticity and fulfillment, you must fight to create more.

 

*If you want to learn more about Alexander von Humboldt, check out The Invention of Nature: Alexander von Humboldt’s New World by Andrea Wulf. It’s a tremendous read and the source of many details in this article.

The 5 Best Books I Read in 2018

Each month I send out a newsletter featuring the best books I’ve worked my way through (I filter out the stuff that sucks). But that list grows quickly and I know it can be tough to decide what to read next. The degree to which a book resonates with you depends largely on the timing of when you read it–what obstacles you’re facing, what skills you’re trying to develop, what your current priorities are.

To provide a more useful starting place, I’ve reflected on the past year and narrowed down my top recommendations to just five books. These are the books that resonated strongest with me at different points in the year and whose lessons remain just as relevant today.

I hope you find something awesome. You can’t go wrong with any of these books. Each is profound and insightful in its own way. If you want to check out my notes before you dive in, click on the book title to see more. Keep up the good reading.

1. The Messy Middle – Scott Belsky
More than a business book, and that’s what I loved about it. It’s about embracing the long game and leading through ambiguity. Whether you’re an entrepreneur or artist, you’ll find relevance. Belsky details the endurance that it takes to bring an idea to life. It might not be as pretty as the beginning or end, but the middle is worthy of equal attention since it’s where most of the journey takes place. Overall, it's a great resource for those who are guiding others (or themselves) through uncertainty. Check out my notes or Amazon for details and reviews.

Curiosity is the fuel you need to play the long game.
— Scott Belsky



2. The Invention of Nature: Alexander von Humboldt's New World – Andrea Wulf
The story of one of the most profound polymaths you've never heard of. Humboldt was a Prussian explorer, writer, geographer, and naturalist born in 1769. He revolutionized the way we view the natural world by making connections and framing nature as a unified whole. He viewed everything as reciprocal and interwoven, challenging the human-centered perspective that ruled up until that point in time (i.e. 'nature is made for the sake of man').

His work also influenced generations of scientists and writers including the likes of Charles Darwin, John Muir, and Henry David Thoreau. It's easy to see why Humboldt was so influential–the stories Wulf tells of his expeditions and adventures well into old age are fascinating. Check out my notes or Amazon for details and reviews.

Nature everywhere speaks to man in a voice familiar to his soul.
— Alexander von Humboldt



3. How to Change Your Mind – Michael Pollan
A look into the renaissance of psychedelics and how a new generation of scientists are testing their potential to improve mental health, including depression, anxiety, trauma, and addiction. Pollan is a brilliant writer, offering a healthy dose of skepticism throughout the book, which helps add a voice of reason to an often fanciful topic. He acknowledges the provocative, often uncomfortable frontier of psychedelic therapy, which sits somewhere between science and spirituality.

True to form, his deep interest in the natural world comes through, specifically as it relates to psilocybin. He also digs into the broader cultural and historical significance, detailing the stories of each influential character involved. But the best parts of the book are when Pollan examines ambiguous, difficult concepts such as consciousness, spirituality, and ego dissolution. Whether you're interested in better understanding the science, potential benefits to mental health, or a new lens through which to view the world and your own experience, this book makes significant contributions to furthering each. Check out my notes or Amazon for details and reviews.

For me, ‘spiritual’ is a good name for some of the powerful mental phenomena that arise when the voice of the ego is muted or silenced.
— Michael Pollan



4. The Inner Game of Tennis – W. Timothy Gallwey
I'm usually skeptical of anything that resembles sports as a metaphor for life, but this a tremendous read. It's less a book about tennis (although there are a few sections) and more about the art of relaxed concentration. It's a simple but profound concept that suggests the secret to performing your best is in developing a quiet confidence, and most importantly, not trying too hard.

Gallwey draws a line between Self 1–the conscious teller, and Self 2–the doer. He advocates developing greater trust in Self 2, which helps to cultivate effortless concentration (flow), instead of a more tense, overly controlled approach which creates an unnecessary obstacle. Gallwey also offers an insightful perspective as he digs deeper into concepts including judgment, ego, and mindfulness, which adds another dimension to the book. Check out my notes or Amazon for details and reviews.

The player of the inner game comes to value the art of relaxed concentration above all other skills; he discovers a true basis for self-confidence; and he learns that the secret to winning any game lies in not trying too hard.
— W. Timothy Gallwey



5. Leonardo da Vinci – Walter Isaacson
The amount of information in this book is incredible (biographies by Walter Isaacson are not quick reads). Throughout the book, I marveled at not only Leonardo, but also Isaacson’s ability to aggregate so much information and tell a compelling story. He’s brilliant at drawing out subtle themes that help tie everything together. Leonardo feels relatable and human in that his genius was self-made, built from personal experience/experiments and dedication to his craft(s). But he feels simultaneously distant in that the breadth of his abilities across disciplines, obsession with detail, and ability to bridge observation and imagination seem otherworldly.

This book is an investment, but you’ll walk away with a reenergized curiosity and a newfound appreciation for the finer details in life. That’s what makes books like this worth it–the message resonates far stronger than what you might get out of a 200-page popular nonfiction title. Check out my notes or Amazon for details and reviews.

“Vision without execution is hallucination...Skill without imagination is barren.”
— Walter Isaacson

Quit Killing Your Team

Most people recognize the importance of hiring. Building something from nothing requires a core team of smart creatives with a deep well of curiosity. These are the innovators who are able to connect ideas between multiple disciplines and offer new ways of looking at the world.

But what’s valued in the hiring process–freethinking, curiosity, creativity–is often forgotten in the day-to-day. And it’s your job to preserve this, for both yourself and your team.

If you want to drive results, you need a better strategy than tightening your grip.

Not everything needs to be about efficiency, productivity, and deliverables. Breathing room helps nurture creativity and curiosity. Those who fail to grasp this nuance end up stuck in a one-track managerial mindset, unable to effectively lead.

Progress comes from having the autonomy to stray into the expanse of your mind and connect ideas in new and interesting ways. Focus on getting the conditions right so everyone has the opportunity to create these connections and find fulfillment in their work.

Without this, you’ll face a barrage of apathy, burnout, and unrealized potential. And once you lose engagement, meaningful progress becomes impossible or short lived.

This is not to say that you shouldn’t set deadlines or establish goals. You need this, too. But if you want to sustain engagement and encourage innovation, allow the people you invested the time to hire to do what set them apart in the first place. Let curiosity and creativity lead the way. This puts your team in a far better position to create something worthwhile.

Leaders fight for a balance between deadlines and exploration.

Designers need freedom to explore creative directions.
Developers need freedom to explore new technologies.
Product managers need freedom to explore different visions.

There’s a sense of artistic expression to each. Creating this space helps build morale by pushing each person to find a deeper sense of satisfaction and meaning in their daily work. It also lays the groundwork for innovation by encouraging people to bridge disciplines, offer new ideas, and test different angles.

This mindset is foundational to every high-performing, rewarding team that I’ve been on. Most recently at Asurion, during a recent year-long effort to drive messaging volume, my team reached a place where we were slowing down and struggling to sustain engagement. To rebuild momentum, we created space to explore how we might leverage a few of our ideas in the smart home–a new space we were all interested in.

We balanced this with our primary initiative, as it wasn’t immediately evident how it would fit in or what was technically feasible. But a few weeks later, we finished building out an Alexa skill which allowed customers to speak with our messaging experts asynchronously via text to speech.

We were able to create something entirely new with the capacity to change how our customers interacted with us. But even if we failed and came out with nothing to show for it, the change of pace held value of its own. It allowed us to reenergize and refocus.

What mattered most was that we gave ourselves space to explore.

There won't always be a one-to-one translation between what you’re exploring and the objective you’re working towards. Sometimes pursuing an idea out of a sense of wonder, is reason enough.

Engaging your curiosity and creativity will help expand your perspective and build momentum. Allow yourself to be distracted from time to time and follow the random ideas that strike your interest, regardless of where they lead.

The most brilliant minds throughout history infused their work with a wandering sense of curiosity.

Leonardo da Vinci embodied this better than anyone else. His entire life followed a series of digressions from his career as an artist.

Leonardo allowed himself to be distracted and seek knowledge for its own sake. This led him to study human anatomy, conduct dozens of dissections, create schemes to divert rivers, choreograph pageants, investigate the flight of birds, and create diagrams of technical innovations such as human flight machines.

Some consider this to be a lack of discipline, which only served to pull him away from more important work. But when you study his life in its entirety, you begin to see how these detours helped shape and inform his art. His obsession with human anatomy, for instance, helped him breathe life into the finest details of his paintings, as he worked from the inside out.

As for the more fantastical detours, such as schematics for flying machines or giant crossbows, I doubt Leonardo would consider this wasted time. It was a channel for his relentless curiosity and creativity–the very things that made him who he was, and a source of pure fulfillment.

Creativity and curiosity are the building blocks of engagement.

Everyone needs space to wander, much like Leonardo, and explore new technology, ideas, and interests. Otherwise, you’ll miss the opportunity to piece together your own insights.

Do you want a team of lemmings going through the motions? Or would you rather have a team that’s imaginative, engaged, and curious?

That’s the difference between driving your team into the ground with a relentless focus on productivity and allowing them breathing room to channel their own creativity.

Your first responsibility is to the people immediately surrounding you–not the product, goals, or traditional measures of productivity. You’ll achieve more in the long run when you have morale, engagement, and innovation on your side.

Authenticity Is Your Now

Authenticity is not a fixed point on a map. It’s fluid, much like your identity, and shifts over the course of your life.

It’s easier to trick yourself into believing the feel-good advice that your voice comes from a sudden revelation. You just have to wait for that moment. And once you’ve found it, the entire picture comes into focus and remains that way for life.

But authenticity is found through fragments. It evolves over time. It’s a moving target that falls out of focus and can be lost to the chaos of life.

Authenticity is less about identifying a singular purpose and voice that should define your entire life. It’s about finding and trusting your voice today. In other words, embracing the impermanence of your identity, knowing that it can and will change.

How you live your life–your interests, principles, and priorities–will evolve over time. As you grow, you’ll add depth to your voice. If you remain the same for too long, that’s when you know you’ve stopped learning or are clinging to an expired version of yourself.

It’s easy to get caught up in the expectations you hold for yourself or that others project upon you– who you should be, where you have been. If you fuel these doubts, you can opt out of the unknown and find comfort in your plateau. But you won’t grow through the familiar, and you won’t find alignment.

Your sense of authenticity–your now–is something that’s all your own. It’s discovered, developed, and deepened, by the obstacles you face, the uncertainties you navigate, and the inspiration you find along the way.

If you want to create something that matters–to both yourself and others–you have to create from where you currently are in your life. That’s how you build momentum and depth. Trust yourself.

It’s the difference between artists and entrepreneurs who get lucky once and those who sustain success over decades. If you cling to what got you there in the first place, you’ll fail to evolve and render yourself irrelevant.

Artists who reinvent themselves fight for projects that allow them to grow, stretch their abilities, and discover new things. In doing so, they create from a place that resonates with them at a single point in time.

Over the course of years, a series of single brush strokes reveals an evolving sense of authenticity.

Bob Dylan, one of history’s great songwriters, has reinvented himself time and time again throughout his career. He’s altered his voice and bridged various genres, beginning in folk, shifting towards rock, and experimenting with country and Christian albums along the way.

Five decades later we can step back and admire his trajectory–how he’s pushed himself to grow, defy expectations, and channel that into his art. Time makes this seem inevitable, as if all he had to do was fall in line with destiny. But that fails to take into account the years of criticism, outrage, and uncertainty Dylan faced.

Authenticity–creating from who you are today, despite expectations tearing you in different directions–is not for the faint of heart.

Dylan threw the folk community into a fit of rage when he “went electric.” He could have stuck with what was working and fallen in line with their expectations, but validation was never his primary motivation. He sought meaning over influence at each step of his career. As a result, he achieved exactly that–lifelong influence.

Dylan resonates with people because his songwriting tracks his own development as a human being. His songs reflect who he was–his observations, experiences, and imagination–and who he refused to be at each point in time. Dylan’s career is a master class in embracing the impermanence of identity and authenticity. The fragments of himself that he brought to life shows he understands this in a deep way.

There were a lot of better singers and better musicians around these places but there wasn’t anybody close in nature to what I was doing. Folk songs were the way I explored the universe...
— Bob Dylan

There’s no single template for finding your voice as it exists today. It’s different for each person. Legendary director, Steven Spielberg, was quite different from Dylan. Dylan had unusual depth which he developed at an early age. Spielberg developed his own sense of depth over decades.

Spielberg’s progression from Jaws (1975) to Schindler’s List (1993) demonstrates this. In those eighteen years, he grew by finding projects that spoke to him at a specific point in time. What felt authentic to him in 1965 was entirely different than 1993. That doesn’t negate his early work, he was just creating from a different place.

Spielberg’s voice evolved through his films, just as Dylan’s did through his albums. That’s why they’ve remained relevant for so many years. They’ve changed, adapted, and grown. But most importantly, both have had the courage to speak from where they were in each present moment.

Both faced criticism along the way for unpopular decisions, but that’s the irony of the whole thing. People are enraged by change, but if you stay the same you guarantee failure. You lose touch with yourself, a sense of fulfillment in your work, and a deeper connection to your audience.

Before you release your work into the wild, fight like hell to make sure it first resonates with you.

No one gets it right each time. There will be times you lose your sense of authenticity. Not even Dylan and Spielberg are immune to the chaos of life. But when the intention and awareness are there, it’s easier to rebuild and rediscover a sense of momentum.

Life is motion. Authenticity is about finding harmony in that motion.

It’s not always easy, but it’s meaningful. Allow yourself to evolve through uncertainty. When you find the courage to speak from this place, you add unusual depth and clarity to your voice. That’s what draws people in.

Start by reflecting on what resonates with you at this point in your life–experiences, interests, observations, values. Authenticity is your now. No matter where you are, trust yourself to create from who you are today.

The Essential Question for Every Entrepreneur

Sometimes the best question you can ask yourself is, "Am I building something I would want?"

As an entrepreneur, this should precede every other question. If the answer is no, there's a fundamental disconnect. You're going to have a difficult time sustaining the necessary effort over the long run. Momentum comes from engagement.

The real secret to product development is creating something that you would want to use.

I evaluate every new product, opportunity, and startup that I consider pursuing with this filter. Success demands years of hard work. If I'm not engaged or I don't find purpose in the work, it's a nonstarter. Otherwise, I know I'll be at a disadvantage facing off against someone solving for their own point of need.

I use the same filter when considering partnerships or investments. I look for founders and teams who are building things they've demonstrated a deep interest in for years.

Consider those who have sustained success over decades–Bill Gates, Sergey Brin, Larry Page, J.K. Rowling, Oprah Winfrey, Bob Dylan, Walt Disney, Albert Einstein, Thomas Edison, Benjamin Franklin. Each person created things they wanted in the world around them. They pursued fields of work they found engaging and compelled to contribute to. That's what kept them going.

And that's the difference between people who burn out or get lucky once and people who sustain success–regardless of industry.

But despite this simple truth, many entrepreneurs insist on building things or addressing problems that they have no real interest in themselves. Most often this is due to inexperience or a lack of integrity.

Inexperience reveals itself in early entrepreneurs who believe that their first decent idea is their only shot at making it. Instead of practicing patience, they force the issue.

But the real currency of successful startups is in execution. You can have the best idea in the world, but if it doesn't resonate with you as an individual, it's going to be difficult to get through the necessary struggles. Creating something from nothing is hard work.

The notion that ideas are a multiplier of execution is empowering. It frees you to be more selective about the startups and projects you get involved with. Instead of looking for a single brilliant idea, look for a strong idea that resonates with you and that you are uniquely suited to bring to life.

There’s no shortage of ideas out there. You might as well take on something you're aligned with and invested in so you feel like you're working towards something worthwhile.

Entrepreneurs with integrity don't involve themselves in projects that aren't aligned with their values and interests. They don't allow themselves to be distracted–even by the allure of easy money. And they don't allow envy to dictate their direction in life.

If you're building something you wouldn't actually want and that you're not proud of, you're sacrificing integrity. And integrity is far harder to come by than money, recognition, or an inflated sense of self-importance. Never mind the ensuing search for lost time.

Your goal in life is to find out the people who need you the most, to find out the business that needs you the most, to find the project and the art that needs you the most. There is something out there just for you. What you don’t want to do is be building checklists and decision frameworks built on what other people are doing. You’re never going to be that. You’ll never be good at being somebody else.
— Naval Ravikant

The world needs more people creating real value–building things that resonate with them and pursuing work that reflects their deepest interests and principles. That's what it takes to build something great and sustain the effort that it takes to overcome inevitable obstacles.

For most hard-working, talented people it’s just a matter of time. Years of consistently showing up, learning, and dedicating time to your craft pays dividends. The power of small, calculated decisions, habits, and behaviors grows exponentially over time.

But first, you must find alignment.

Are you building something because you think someone else might want it?

Or are you creating something that you would actually want to use? This reflects a deeper interest and resilience. It's an immediate advantage that puts you in a far better position to succeed. This is where you want to be.

The Four Elements of Becoming a Better Writer

There's nothing that writers love more than reading about writing (although, reading about reading comes in at a close second). Everyone's looking for a universal secret that sets apart the best writers or makes the writing process easier. Unfortunately, that secret doesn't exist.

The only consistency I have found across all great writers is that they show up. They define themselves by an insatiable desire to write–it's a core part of their routine and they put in the work every single day. 

While you might not self-identify as a "writer," that's okay. Journaling for reflection, working on your communication skills, and piecing together a 300-page novel are each valid objectives. But if you want to improve your writing–the foundational skill to each of these–you have to consistently show up, work at it, and make it part of your routine.

Over the past year, quite a few people have reached out asking for details on my own writing process. While I consider my writing skills to be a work in progress, this is my attempt to detail what my current system looks like. I don't pretend to have all the answers, but my hope is to provide you with a few tactics that you might leverage on your own.

Takeaways:

  1. Reading, writing and learning fuel each other. Channel your intellectual curiosity and you'll never face a shortage of ideas.

  2. Timing is important but it's not everything. Determine what's sustainable for you and stick with that.

  3. Writing is about momentum and a relaxed state of concentration. Don't interrupt this unnecessarily.

  4. Editing demands grit. It's here where the great writers set themselves apart.


How do you come up with ideas?

Reading, writing, and learning fuel each other. Anytime I've struggled to come up with new ideas, it's almost always because I'm not reading enough or challenging myself to learn anything new. If you channel your intellectual curiosity, this problem takes care of itself. 

Read, listen to podcasts, make sure you're learning something new in every environment you're in. This is how you begin building a network of mental models which allows you to uncover new ideas and connect concepts in interesting ways.

When you commit time to pursue knowledge and exercise your own curiosity–in whatever form that takes–you'll never face a shortage of new material and ideas to choose from. 

I keep a running list of all my ideas, potential topics, and relevant thoughts in Notes (iOS) and Ulysses. This way I don't lose track of anything that comes to me throughout the day. 

When do you write?

Timing is important, but it's not everything. It can either be an excuse to avoid putting in the work, or it can be turned to your advantage. While many great writers have tended to write early in the morning, you shouldn't obsess over replicating their routines. Find what works and is sustainable, for you. The most important thing is getting started.

Once you're in the habit of writing, if you want to fine-tune your process, consider your internal clock. Writing is an intensive, creative process that demands significant focus. If at all possible, pick a time of the day when you're at your peak level of concentration. Otherwise, it will be tough to sustain.

I'm a morning person–my most productive hours are between 6:30 and 10:30 AM. Each morning I wake up at 6:00 AM and write for at least a couple hours before heading into work. I guard this time seven days a week, as it's the most important part of the day for me. Weekends are slightly different, with a few hours of writing in the morning, and a second shorter session at a coffee shop in the afternoon. 

This will inevitably change over time as your position in life changes. Five years ago, I was the exact opposite and only wrote at night. Allow yourself to adapt, but make sure you don't lose the habit.

What does your writing process look like?

Sometimes I begin writing an article because I have a general idea of what I want to say. Other times, I'm trying to figure something out for myself. Either way, for me, writing is about momentum.

When I sit down to work through a new idea, I'm not writing for structure or format. I'm not writing to assemble a cohesive argument. And I'm not writing from an outline. I'm writing to get every relevant thought I have on that topic down on paper. For a single article, this can take anywhere from an hour to a few days.

The motivation during this initial phase is to get to a place where I'm not thinking about the act of writing. If I start thinking too much about what I'm doing, I can't achieve a state of relaxed concentration where I am at my most creative and coming up with my best work.

As one achieves focus, the mind quiets. As the mind is kept in the present, it becomes calm. Focus means keeping the mind now and here. Relaxed concentration is the supreme art because no art can be achieved without it.
— W. Timothy Gallwey

Other than my initial approach, I've found a couple of tactics that help facilitate this momentum, flow, relaxed concentration–whatever you want to call it. 

The first is that I'll listen to the same song for hours on end to help induce a deeper state of creativity. I've found that listening to one song on repeat often helps jumpstart things and push me towards the proper state of mind. I'm not the first one to discover this, it seems quite popular among writers and software developers.

The second tactic I use is to help steal some sense of momentum when things have stalled. To overcome inevitable lulls, I'll double back and rewrite the previous sentence or two. It's a mental thing where I feel like I can carry that energy through better if I'm able to create some type of forward motion.

Think of it as riding your bike up a hill. If you mount your bike in the middle of a hill, it can be difficult to make your way to the top based on the immediate level of resistance. Whereas if you start at the bottom (less resistance) and build some momentum going into the climb, you'll be able to better carry that through to the top. It's amazing how often this gets me back on track heading into a new section. 


How do you edit/refine your articles?

This is where the attention to detail comes into play. My rough drafts are very rough drafts. As a result, I spend a significant amount of time editing, rewriting, and refining.

After I have all my thoughts down, I go back through the material to identify common themes and distill the most important ideas. Certain insights may (or may not) appear, and I'll draw from those as I begin to organize the article. 

I'm never finished writing at this point. Often, there's quite a bit of work to be done. After I've arranged the article and developed some sense of structure, I'll go back and immerse myself in certain sections so I'm able to simplify ideas. Again, if I get stuck I'll use the tactics mentioned above to capture the same sense of flow I had during the initial writing process. 

This part of the creative process often feels similar to a puzzle. You're piecing together fragments and determining how they best fit together. And it's in the process of uncovering and assembling those fragments that you find yourself and your best ideas in.

From the outside, writing appears romantic. You just pour your ideas onto a page then call it a day. But those who live it know the grit it entails. The editing process demands the greatest persistence of all. And it's never something you can rush through.

Grit entails working strenuously toward challenges, maintaining effort and interest over years despite failure, adversity, and plateaus in progress. The gritty individual approaches achievement as a marathon, his or her advantage is stamina. Whereas disappointment or boredom signals to others that it is time to change trajectory and cut losses, the gritty individual stays the course.
— Angela Duckworth

No one is above this final piece of the writing process–not even the greats. Ernest Hemingway rewrote the ending of A Farewell to Arms 47 times. Harper Lee spent two years working with her editor, Tay Hohoff, reworking the entire plot and cast of characters in what would become To Kill A Mockingbird

It's foolish to expect perfection each time you sit down to write. If you get to the point where you've stared at what you've written for too long and begin to hate it, step away for a few days. Time and distance are often the true tests of quality.

But regardless of your objective, the most important part is sitting down to practice the craft.

Writing is not about some stroke of genius and it’s not pretty. It’s about grit, showing up, writing, editing, rewriting, and refining.